No one looks forward to having a difficult conversation. Whether you’re conducting or responding to a performance evaluation at work, comforting a bereaved friend, or discussing a behavioral issue with a family member, there are five steps that can help to change these “confrontations” into “communication.”

Don’t put off the discussion to the “perfect moment.”

Waiting for the “right” opportunity to raise a difficult issue is counter-productive in two ways. It allows you to postpone the inevitable, and it creates excuses for why not to say something. “It’s too late (or too early) in the day,” just allows the discussion to be put off for no real reason. “She seems to be in a bad mood and won’t want to talk about this,” is basing your hesitation on an assumption about someone else’s mindset. My favorite is, “I think I’m coming down with something and can’t think straight.” That one’s self explanatory.

Just say something.

Like the perfect moment, the need for the perfect words is a delay tactic. No one really has the perfect words, especially in situations where someone is suffering a loss or disappointment. The best thing is say is . . . something. How about saying “I was thinking about you,” or asking “Do you want to take a walk?” Almost anything that allows communication to begin is beneficial. Someone in emotional pain may not want to address the issue head on, but would appreciate a kind word. In a work-related conversation, the best approach might be a direct: “How can I help you to improve your work performance?

Don’t try to fix things – just acknowledge.

Sometimes, a solution isn’t necessary, or even wanted. The best way to address that fact is to open the communication and then just listen. I learned this the hard way, when one of my then-high-school aged children was telling me about a problem at school. I (of course) jumped in with a number of fix-its that could be implemented immediately. His response was “I don’t need you to fix this. I just need you to listen.”

Commit to a follow-up.

One of the most important things about the difficult conversation is determining what to do after it has been conducted. If the conversation is work-related, maybe agreeing to a regular meeting/discussion would be beneficial. After comforting a sad friend, agreeing to meet for coffee or lunch is often a follow-up that shows continued interest and willingness to help. The point is to show a commitment to continue the discussion, and a genuine interest in improving the situation.


Obviously, if you commit to a follow-up, the important next step is to act on that. Nothing will undermine your credibility faster than beginning a difficult conversation, making headway on the issues, agreeing to do something to improve the situation, and then, doing nothing. Be mindful of the effect that your discussions are having on the other person. Your actual commitment to continue the communication is a critical element is resolving the original issue.

The stakes typically are high in difficult conversations, which is, of course, one of the reasons that we avoid them. But the payoff is huge. Having these types of discussions takes courage and mindful empathy – two leadership skills acknowledged as valuable and critical to today’s fast-paced environment. Initiating difficult discussions in a thoughtful and non-emotional way also helps to hone problem-solving skills, another leadership quality.

There are a number of thoughtful and helpful articles and resources to consult that may help you to implement these five steps. But like everything else that’s worth learning, you won’t get good at conducting difficult conversations unless you practice handling them, both at work and at home. Start with the five steps listed, and move forward from there.